99365-40-9Relevant articles and documents
Synthesis and photophysical characterization of isoindigo building blocks as molecular acceptors for organic photovoltaics
Din?alp, Haluk,Saltan, G?zde Murat,Zafer, Ceylan,Mutlu, Adem
, p. 196 - 206 (2018)
Five isoindigo-based donor-acceptor-donor (D-A-D) type small molecules have been synthesized in order to investigate their intramolecular charge transfer characteristics. UV–vis absorption of these dyes exhibits a wide absorption band ranging from 300 to 650 nm with two distinct bands, giving the narrow bandgaps between 1.72 and 1.85 eV. Taking into account their HOMO-LUMO energy levels and bandgaps, isoindigo dyes have been used in the active layer of organic solar cell (OSC) devices. When these small molecule semiconductors were used as acceptors with the donor poly(3-hexylthiophene-2,5-diyl (P3HT) polymer in the inverted OSC devices, the highest power conversion efficiency (PCE) was obtained as 0.10% for pyrene-substituted isoindigo derivative.
Novel calamitic liquid crystalline organic semiconductors based on electron-deficient dibenzo[: C, h] [2,6]naphthyridine: Synthesis, mesophase, and charge transport properties by the time-of-flight technique
Yang, Ming-Cong,Hanna, Jun-Ichi,Iino, Hiroaki
, p. 13192 - 13202 (2019/11/13)
Calamitic liquid crystalline organic semiconductors based on an electron-deficient dibenzo[c,h][2,6]naphthyridine (DBN) core were designed for electron transport materials and synthesized from 6-bromoisatin to form a key intermediate without tedious purification by means of a one-pot reaction including 4 steps, and then the target products were obtained in an additional 3 steps in a total yield of 13%. Two dialkylated DBN derivatives, 2,8-didecyl DBN (C10-DBN-C10) and 2,8-didodecyl DBN (C12-DBN-C12), exhibited a low ordered mesophase of smectic C (SmC) only. Their phase transitions, photophysical properties, and charge carrier transport properties were investigated and compared with their carbon analogs, i.e., chrysene and the DBN isomers of isoquino[8,7-h]isoquinoline derivatives. In the SmC phase, transient photocurrents had well-defined transits, which allowed us to evaluate their exact mobilities. The mobility for negative and positive carriers in the SmC phase depended on both electric field and temperature, which suggested that the conduction mechanism is via electronic hopping transport for both holes and electrons. It was unexpectedly found that C10-DBN-C10 in the SmC phase exhibited quite low mobility on the order of 10-5 cm2 V-1 s-1, which is two orders of magnitude smaller than that for dialkylated chrysenes, and is comparable to the typical mobility in liquid crystalline semiconductors with large dipole moments, even though the DBN core has no dipole moment; this is also true for holes. This new phenomenon has not been reported before, and may provide new insight into how mobility in liquid-crystal phases is determined.
Polymer based on benzothiadiazole-bridged bis-isoindigo for organic field-effect transistor applications
Deng, Ping,Li, Shugang,Wu, Jian,Zhang, Qing,Lei, Yanlian,Zhu, Furong,Zheng, Xuelin,Ong, Beng S.
, p. 407 - 413 (2015/12/30)
Two isoindigos were symmetrically connected by 2,1,3-benzothiadiazole core to form an acceptor2-acceptor1-acceptor2 monomer. The new monomer was used as electron acceptor unit in construction of a unique donor/acceptor polymer with donor-acceptor2-accepto
